RU2009105818A - Пиразолы в качестве активаторов глюкокиназы - Google Patents

Пиразолы в качестве активаторов глюкокиназы Download PDF

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Publication number: RU2009105818A
Authority: RU; Russia
Prior art keywords: group; pyrazol; hydroxy; compound; propionamide
Prior art date: 2006-07-24

Application number

RU2009105818/04A

Other languages

English (en)

Russian (ru)

Inventor

Стивен Джозеф БЕРТЕЛ (US)

Стивен Джозеф Бертел

Роберт Франсис КЕСТЕР (US)

Роберт Франсис Кестер

Дуглас Эрик МАРФИ (US)

Дуглас Эрик МАРФИ

Томас Джей ПРИНС (US)

Томас Джей ПРИНС

Франк РЬЮБСАМ (US)

Франк РЬЮБСАМ

Рамакант САРАБУ (US)

Рамакант Сарабу

Чин Вьет ТРАН (US)

Чин Вьет Тран

Дионисиос ВОУРЛОУМИС (GR)

Дионисиос ВОУРЛОУМИС

Original Assignee

Ф.Хоффманн-Ля Рош Аг (Ch)

Ф.Хоффманн-Ля Рош Аг

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-07-24

Filing date

2007-07-16

Publication date

2010-08-27

2007-07-16 Application filed by Ф.Хоффманн-Ля Рош Аг (Ch), Ф.Хоффманн-Ля Рош Аг filed Critical Ф.Хоффманн-Ля Рош Аг (Ch)

2010-08-27 Publication of RU2009105818A publication Critical patent/RU2009105818A/ru

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102000030595 Glucokinase Human genes 0.000 title 1
108010021582 Glucokinase Proteins 0.000 title 1
239000012190 activator Substances 0.000 title 1
150000003217 pyrazoles Chemical class 0.000 title 1
-1 perfluoro Chemical group 0.000 claims abstract 113
125000000217 alkyl group Chemical group 0.000 claims abstract 56
150000001875 compounds Chemical class 0.000 claims abstract 45
229910052739 hydrogen Inorganic materials 0.000 claims abstract 41
239000001257 hydrogen Substances 0.000 claims abstract 41
125000003545 alkoxy group Chemical group 0.000 claims abstract 16
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 14
125000003277 amino group Chemical group 0.000 claims abstract 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 9
229910052736 halogen Inorganic materials 0.000 claims abstract 9
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 8
150000002367 halogens Chemical class 0.000 claims abstract 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims abstract 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
125000003342 alkenyl group Chemical group 0.000 claims abstract 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 claims abstract 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
CJZFOZAQGBLEFL-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene 1-oxide Chemical compound C1=CC=C2S(=O)CCCC2=C1 CJZFOZAQGBLEFL-UHFFFAOYSA-N 0.000 claims abstract 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 2
125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract 2
150000001602 bicycloalkyls Chemical group 0.000 claims abstract 2
125000005842 heteroatom Chemical group 0.000 claims abstract 2
125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
229910052760 oxygen Inorganic materials 0.000 claims abstract 2
229910052717 sulfur Inorganic materials 0.000 claims abstract 2
150000002431 hydrogen Chemical class 0.000 claims 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
229910052801 chlorine Inorganic materials 0.000 claims 8
239000000460 chlorine Substances 0.000 claims 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 6
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 5
229940080818 propionamide Drugs 0.000 claims 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 4
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 3
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 3
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 3
125000003282 alkyl amino group Chemical group 0.000 claims 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
208000030159 metabolic disease Diseases 0.000 claims 3
238000000034 method Methods 0.000 claims 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
125000002757 morpholinyl group Chemical group 0.000 claims 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
229920001774 Perfluoroether Chemical group 0.000 claims 2
239000013543 active substance Substances 0.000 claims 2
206010012601 diabetes mellitus Diseases 0.000 claims 2
125000004663 dialkyl amino group Chemical group 0.000 claims 2
230000002503 metabolic effect Effects 0.000 claims 2
125000003566 oxetanyl group Chemical group 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
DVUBKGBRRZEPHE-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclobutyl-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 DVUBKGBRRZEPHE-MRXNPFEDSA-N 0.000 claims 1
XWVHADYSFYQROQ-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-(1-ethylpyrazol-3-yl)propanamide Chemical compound CCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 XWVHADYSFYQROQ-MRXNPFEDSA-N 0.000 claims 1
XLEVHMJYBIWAEH-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 XLEVHMJYBIWAEH-QGZVFWFLSA-N 0.000 claims 1
LQJXAPFIVCRJQZ-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(2-hydroxyethyl)pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CCO)C=C1)CC1CCCC1 LQJXAPFIVCRJQZ-MRXNPFEDSA-N 0.000 claims 1
QJYSUBVDZHQKPS-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(2-methoxy-2-methylpropyl)pyrazol-3-yl]propanamide Chemical compound COC(C)(C)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 QJYSUBVDZHQKPS-GOSISDBHSA-N 0.000 claims 1
PZEKJMLNXJVMJF-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(2-methoxyethyl)pyrazol-3-yl]propanamide Chemical compound COCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 PZEKJMLNXJVMJF-QGZVFWFLSA-N 0.000 claims 1
CMLBDGASMRNGJZ-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(3-hydroxypropyl)pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CCCO)C=C1)CC1CCCC1 CMLBDGASMRNGJZ-QGZVFWFLSA-N 0.000 claims 1
LVGYTGUYABTAAL-LJQANCHMSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(3-methylbutyl)pyrazol-3-yl]propanamide Chemical compound CC(C)CCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 LVGYTGUYABTAAL-LJQANCHMSA-N 0.000 claims 1
WOKAHPPHKMQUHO-GOSISDBHSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(cyclopropylmethyl)pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CC2CC2)C=C1)CC1CCCC1 WOKAHPPHKMQUHO-GOSISDBHSA-N 0.000 claims 1
UBMSEKYTKWFEQC-QGZVFWFLSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-[(1-hydroxycyclopropyl)methyl]pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CC2(O)CC2)C=C1)CC1CCCC1 UBMSEKYTKWFEQC-QGZVFWFLSA-N 0.000 claims 1
WAVSARMTMVZFJV-IAGOWNOFSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-[(2r)-2,3-dihydroxypropyl]pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(C[C@@H](O)CO)C=C1)CC1CCCC1 WAVSARMTMVZFJV-IAGOWNOFSA-N 0.000 claims 1
WAVSARMTMVZFJV-DLBZAZTESA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-[(2s)-2,3-dihydroxypropyl]pyrazol-3-yl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(C[C@H](O)CO)C=C1)CC1CCCC1 WAVSARMTMVZFJV-DLBZAZTESA-N 0.000 claims 1
IKGMOWROQTUWQE-JOCHJYFZSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-[(4-methylsulfonylphenyl)methyl]pyrazol-3-yl]propanamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1N=C(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)C=C1 IKGMOWROQTUWQE-JOCHJYFZSA-N 0.000 claims 1
NKFAAXUNSBBBCU-MRXNPFEDSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]-3-(3-oxocyclobutyl)propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CC(=O)C2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 NKFAAXUNSBBBCU-MRXNPFEDSA-N 0.000 claims 1
AICNHVFQVHKPAL-XJKSGUPXSA-N (2r)-2-(3-chloro-4-methylsulfonylphenyl)-n-[1-(2-hydroxyethyl)pyrazol-3-yl]-3-[(1r)-3-oxocyclopentyl]propanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CCO)C=C1)C[C@@H]1CC(=O)CC1 AICNHVFQVHKPAL-XJKSGUPXSA-N 0.000 claims 1
SOYWWPLNYRCBBK-GOSISDBHSA-N (2r)-2-(3-cyano-4-methylsulfonylphenyl)-3-cyclopentyl-n-[1-(2-hydroxyethyl)pyrazol-3-yl]propanamide Chemical compound C1=C(C#N)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CCO)C=C1)CC1CCCC1 SOYWWPLNYRCBBK-GOSISDBHSA-N 0.000 claims 1
KIEWDROTUPACRI-MRXNPFEDSA-N (2r)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(Cl)=CC=2)=N1 KIEWDROTUPACRI-MRXNPFEDSA-N 0.000 claims 1
BIUKLLVBIWEFRD-OAHLLOKOSA-N (2r)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-[1-(2-hydroxyethyl)pyrazol-3-yl]propanamide Chemical compound OCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(Cl)=CC=2)=N1 BIUKLLVBIWEFRD-OAHLLOKOSA-N 0.000 claims 1
CPBVFRMDMXUZFK-MRXNPFEDSA-N (2r)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-[1-(2-methoxyethyl)pyrazol-3-yl]propanamide Chemical compound COCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(Cl)=CC=2)=N1 CPBVFRMDMXUZFK-MRXNPFEDSA-N 0.000 claims 1
CZTHKQUQMYEQNZ-MRXNPFEDSA-N (2r)-3-cyclopentyl-2-(3,4-dichlorophenyl)-n-[1-(3-hydroxypropyl)pyrazol-3-yl]propanamide Chemical compound OCCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(Cl)=CC=2)=N1 CZTHKQUQMYEQNZ-MRXNPFEDSA-N 0.000 claims 1
COWUKNBFYBTNEW-OAQYLSRUSA-N (2r)-3-cyclopentyl-2-(4-cyclopropylsulfonylphenyl)-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=CC(=CC=2)S(=O)(=O)C2CC2)=N1 COWUKNBFYBTNEW-OAQYLSRUSA-N 0.000 claims 1
SCSCGKBPWURDSH-LJQANCHMSA-N (2r)-3-cyclopentyl-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]-2-(4-methylsulfonylphenyl)propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 SCSCGKBPWURDSH-LJQANCHMSA-N 0.000 claims 1
BQAINONJIKHQIS-GOSISDBHSA-N (2r)-3-cyclopentyl-n-[1-(2-hydroxy-2-methylpropyl)pyrazol-3-yl]-2-[3-(trifluoromethyl)phenyl]propanamide Chemical compound CC(C)(O)CN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(C=CC=2)C(F)(F)F)=N1 BQAINONJIKHQIS-GOSISDBHSA-N 0.000 claims 1
GUPJZDOYGBNXNI-GOSISDBHSA-N (2r)-3-cyclopentyl-n-[1-(2-hydroxyethyl)pyrazol-3-yl]-2-(3-methyl-4-methylsulfonylphenyl)propanamide Chemical compound C1=C(S(C)(=O)=O)C(C)=CC([C@@H](CC2CCCC2)C(=O)NC2=NN(CCO)C=C2)=C1 GUPJZDOYGBNXNI-GOSISDBHSA-N 0.000 claims 1
IIGRLNXVIHPREF-LJQANCHMSA-N (2r)-3-cyclopentyl-n-[1-(2-methoxyethyl)pyrazol-3-yl]-2-(3-methyl-4-methylsulfonylphenyl)propanamide Chemical compound COCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(C)C(=CC=2)S(C)(=O)=O)=N1 IIGRLNXVIHPREF-LJQANCHMSA-N 0.000 claims 1
VEYMDPJRGMPTPX-GOSISDBHSA-N (2r)-3-cyclopentyl-n-[1-(2-methoxyethyl)pyrazol-3-yl]-2-[3-(trifluoromethyl)phenyl]propanamide Chemical compound COCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(C=CC=2)C(F)(F)F)=N1 VEYMDPJRGMPTPX-GOSISDBHSA-N 0.000 claims 1
JSCGIDBYKFGCLP-LJQANCHMSA-N (2r)-3-cyclopentyl-n-[1-(3-hydroxypropyl)pyrazol-3-yl]-2-(3-methyl-4-methylsulfonylphenyl)propanamide Chemical compound C1=C(S(C)(=O)=O)C(C)=CC([C@@H](CC2CCCC2)C(=O)NC2=NN(CCCO)C=C2)=C1 JSCGIDBYKFGCLP-LJQANCHMSA-N 0.000 claims 1
ZWJKEICCOCTMML-GOSISDBHSA-N (2r)-3-cyclopentyl-n-[1-(3-hydroxypropyl)pyrazol-3-yl]-2-[3-(trifluoromethyl)phenyl]propanamide Chemical compound OCCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(C=CC=2)C(F)(F)F)=N1 ZWJKEICCOCTMML-GOSISDBHSA-N 0.000 claims 1
KZARIHGSUISYBH-OAQYLSRUSA-N (2r)-n-(1-benzylpyrazol-3-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1[C@H](C(=O)NC1=NN(CC=2C=CC=CC=2)C=C1)CC1CCCC1 KZARIHGSUISYBH-OAQYLSRUSA-N 0.000 claims 1
HCXMPLFDXOVCGK-GOSISDBHSA-N (2r)-n-(1-butylpyrazol-3-yl)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanamide Chemical compound CCCCN1C=CC(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)=N1 HCXMPLFDXOVCGK-GOSISDBHSA-N 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
FRJNKYGTHPUSJR-UHFFFAOYSA-N 1-benzothiophene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)C=CC2=C1 FRJNKYGTHPUSJR-UHFFFAOYSA-N 0.000 claims 1
NKPTVQFJWGCELJ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)CCC2=C1 NKPTVQFJWGCELJ-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
WQSKQNNAFCZORQ-JOCHJYFZSA-N 3-[[3-[[(2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanoyl]amino]pyrazol-1-yl]methyl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(CN2N=C(NC(=O)[C@H](CC3CCCC3)C=3C=C(Cl)C(=CC=3)S(C)(=O)=O)C=C2)=C1 WQSKQNNAFCZORQ-JOCHJYFZSA-N 0.000 claims 1
ZFTXZVPMMPUDIN-RUZDIDTESA-N 4-[[3-[[(2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanoyl]amino]pyrazol-1-yl]methyl]-n-(3-methoxypropyl)benzamide Chemical compound C1=CC(C(=O)NCCCOC)=CC=C1CN1N=C(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)C=C1 ZFTXZVPMMPUDIN-RUZDIDTESA-N 0.000 claims 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000003993 interaction Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
BPZXPHHRZVFGOQ-QETWGEEDSA-N methyl 4-[[3-[[(2r)-2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentylpropanoyl]amino]pyrazol-1-yl]methyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CN1N=C(NC(=O)[C@H](CC2CCCC2)C=2C=C(Cl)C(=CC=2)S(C)(=O)=O)C=C1 BPZXPHHRZVFGOQ-QETWGEEDSA-N 0.000 claims 1
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
229940124530 sulfonamide Drugs 0.000 abstract 1
UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

RU2009105818/04A 2006-07-24 2007-07-16 Пиразолы в качестве активаторов глюкокиназы RU2009105818A (ru)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US83290706P	2006-07-24	2006-07-24
US60/832,907		2006-07-24
US93081907P	2007-05-18	2007-05-18
US60/930,819		2007-05-18

Publications (1)

Publication Number	Publication Date
RU2009105818A true RU2009105818A (ru)	2010-08-27

Family

ID=38657003

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RU2009105818/04A RU2009105818A (ru)	2006-07-24	2007-07-16	Пиразолы в качестве активаторов глюкокиназы

Country Status (16)

Country	Link
US (1)	US7935699B2 (fr)
EP (2)	EP2046755A2 (fr)
JP (1)	JP2009544648A (fr)
KR (1)	KR20090025358A (fr)
AR (1)	AR062012A1 (fr)
AU (1)	AU2007278261A1 (fr)
BR (1)	BRPI0715531A2 (fr)
CA (1)	CA2657566A1 (fr)
CL (1)	CL2007002121A1 (fr)
IL (1)	IL196321A0 (fr)
MX (1)	MX2009000688A (fr)
NO (1)	NO20090064L (fr)
PE (1)	PE20080406A1 (fr)
RU (1)	RU2009105818A (fr)
TW (1)	TWI332948B (fr)
WO (1)	WO2008012227A2 (fr)

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2007
- 2007-07-16 JP JP2009521210A patent/JP2009544648A/ja active Pending
- 2007-07-16 WO PCT/EP2007/057315 patent/WO2008012227A2/fr not_active Ceased
- 2007-07-16 EP EP07787582A patent/EP2046755A2/fr not_active Withdrawn
- 2007-07-16 CA CA002657566A patent/CA2657566A1/fr not_active Abandoned
- 2007-07-16 KR KR1020097001515A patent/KR20090025358A/ko not_active Ceased
- 2007-07-16 EP EP10175986A patent/EP2261216A3/fr not_active Withdrawn
- 2007-07-16 BR BRPI0715531-0A2A patent/BRPI0715531A2/pt not_active IP Right Cessation
- 2007-07-16 MX MX2009000688A patent/MX2009000688A/es not_active Application Discontinuation
- 2007-07-16 AU AU2007278261A patent/AU2007278261A1/en not_active Abandoned
- 2007-07-16 RU RU2009105818/04A patent/RU2009105818A/ru not_active Application Discontinuation
- 2007-07-19 US US11/879,935 patent/US7935699B2/en not_active Expired - Fee Related
- 2007-07-20 AR ARP070103249A patent/AR062012A1/es not_active Application Discontinuation
- 2007-07-20 TW TW096126648A patent/TWI332948B/zh not_active IP Right Cessation
- 2007-07-20 CL CL200702121A patent/CL2007002121A1/es unknown
- 2007-07-23 PE PE2007000954A patent/PE20080406A1/es not_active Application Discontinuation
2009
- 2009-01-01 IL IL196321A patent/IL196321A0/en unknown
- 2009-01-06 NO NO20090064A patent/NO20090064L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
MX2009000688A (es)	2009-01-30
WO2008012227A2 (fr)	2008-01-31
CA2657566A1 (fr)	2008-01-31
BRPI0715531A2 (pt)	2014-06-24
AU2007278261A1 (en)	2008-01-31
PE20080406A1 (es)	2008-04-28
TW200812974A (en)	2008-03-16
EP2261216A3 (fr)	2011-12-14
WO2008012227A8 (fr)	2008-09-12
WO2008012227A3 (fr)	2008-05-15
AR062012A1 (es)	2008-08-10
EP2046755A2 (fr)	2009-04-15
US7935699B2 (en)	2011-05-03
EP2261216A2 (fr)	2010-12-15
KR20090025358A (ko)	2009-03-10
IL196321A0 (en)	2009-09-22
CL2007002121A1 (es)	2008-02-22
JP2009544648A (ja)	2009-12-17
NO20090064L (no)	2009-02-04
US20080021032A1 (en)	2008-01-24
TWI332948B (en)	2010-11-11

Publication	Publication Date	Title
RU2009105818A (ru)	2010-08-27	Пиразолы в качестве активаторов глюкокиназы
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